Ammonia → HCID 15228051, compound

HRID 1653694Notes

Reaction equation

HRID 1653694 reaction equation
[CH:1]1[C:10]2[C:5](=[C:6]([NH:11][C:12]3[C:13](=[O:20])[C:14](=[O:19])[C:15]=3OCC)[CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1.[NH3:21]>C(O)C>[NH2:21][C:15]1[C:14](=[O:19])[C:13](=[O:20])[C:12]=1[NH:11][C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:5]=1[CH:4]=[CH:3][N:2]=[CH:1]2

Participants

4

Reactant 2

HCID 222AmmoniaHCID 108018323-(Isoquinolin-5-ylamino)-4-ethoxy-cyclobut-3-ene-1,2-dione

Product 1

HCID 15228051HCID 15228051, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
45 °C

Procedure

A suspension of the the product from Example 8, Step 1 (0.190 g, 0.700 mmol) in ethanol (3.5 mL) was saturated with ammonia, capped, and heated to 45° C. for three hours. The mixture was cooled, concentrated, and triturated with diethylether. Crude product was recrystallized from dimethylformamide/water to give 0.129 g (77%) of the title compound as a pale yellow solid, one-eighth hydrate: mp 215° C.; 1H NMR (DMSO-d6): δ9.87 (s, 1H), 9.34 (s, 1H), 8.60 (d, 1H), 7.40-8.60 (broad signal, NH2), 8.02 (d, 1H), 7.86 (d, 1H), 7.77 (d, 1H), 7.68 (t, 1H). IR (KBr): 3200, 1800, 1690, 1650 cm-1 ; MS (m/z) 240(MH+).

Workup

  1. customcapped
  2. temperatureThe mixture was cooled
  3. concentrationconcentrated
  4. customtriturated with diethylether
  5. customCrude product was recrystallized from dimethylformamide/water

Sources & evidence

ORD record
ord-471b585330fd4a03b4b9cedeef057be5
Source dataset
uspto-grants-1995_04
Patent number
US05403854

Reaction notes

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